Watching You
by Winchester84
Summary: She can’t explain it, and she doesn’t want to, but there is just something alluring about the older Winchester brother that draws her to him. xDean/Rubyx


**Title:** Watching You  
**Author:** winchester84  
**Fandom:** SPN  
**Pairing:** Dean/Ruby  
**Rated:** R  
**Genre:** Drama, Sort of AU I guess...  
**Summary:** She can't explain it, and she doesn't want to, but there is just something alluring about the older Winchester brother that draws her to him.

**Disclaimer:** None of this is mine, and none of what you are about to read has happened in real life, obviously.

* * *

**Watching You**

Covered in shadow Ruby watches as the Winchester's drink their coffee and scour the newspaper for the next hunt. Both look so nonchalant as they sit at a black metal table, not even realizing that they are being watched. Sam looks to be in deep concentration as he reads an article from the newspaper in his hands while Dean simply appears to be bored, glancing around them, tapping his fingers on the metal table, bouncing his leg, dropping his chin into one of his awaiting palms. From years of practice, Sam ignores his brother and studiously gives his attention to their next possible hunt.

The young hunter seems oblivious to anything around him, which Ruby would tell him isn't a smart thing to do, for a hunter, if she were willing to give herself away right now. She isn't willing to, though, is content with keeping watch from afar. He doesn't know that she is here, looking out for him, but she knows he suspects it at the very least. He is her messiah, she is never very far from where he is, and she has a feeling he is beginning to understand that. She has to make sure nothing happens to him, after all. They can't possibly expect to win this war without him.

It is almost inevitable when her eyes slide over to Dean. She can't explain it, and she doesn't want to, but there is just something alluring about the older Winchester brother that draws her to him. She can't help but hate herself a little for it because, _damn it_, she isn't supposed to be so captivated by a human, much less a walking dead one at that. She finds herself captivated by him, though, and she can't seem to stay away from him no matter how many times she tells herself to do so.

As she stands there, hidden in the shadows, she watches Dean intently and tries to figure out what it is she finds so damn fascinating about him. What is so damn special about **him** that she can't draw away from him? Looking at him, all she sees is a regular guy, with nothing different from any other human she's come across. Yet, there also seems to be something irresistible about him, as well... she just can't figure out what it is.

Dean doesn't have much time left, in a few months he'll be on his one way ticket to hell and Ruby won't have to be bothered by him anymore. This should cheer her up, bring her to her senses, but instead all it does is leave her feeling hollow and numb inside. _That's strange_, she thinks to herself as she studies these strange feelings. _What the hell is Dean Winchester doing to me?_

۞ ۞ ۞

Ruby steps back into the shadows when the door to the Winchester's motel room opens and Dean steps out. It is the middle of the night, she's sure Sam is sound asleep by now, so where is the hunter going? She watches as he bypasses the Impala, not even appearing to consider getting inside, and crosses the barren street as though he doesn't have a care in the world.

When he is a safe distance ahead of her, Ruby steps out of concealment and quietly follows the hunter down the dark street. She stays at a distance so he won't see her but remains close enough to not lose sight of him. As she follows him down a desolate dirt road, getting dust all over her boots, she feels like groaning in frustration. Why is she even bothering herself with him? Why is she following him blindly to some place unknown? She honestly doesn't know but she follows him nonetheless.

Before long they come upon an old bridge that appears to have seen better days and Dean stops walking once he reaches it. He leans his arms on the old wooden railing and from where Ruby stands she can hear it give off a loud creak from his weight and she briefly wonders if it will give way at any second. Ruby stands back at a safe distance, not giving any indication of her presence, and Dean gives off no signs that he can sense her.

From where she stands, she watches as he releases a heavy, burdened sigh, and lowers his head to stare at the calm water of the river below. The moon rests high in the sky, giving off just a bit of light, but not enough for the human eye to see much through the darkness. Being a demon has its advantages; she can see his every feature clearly.

From his facial features alone she can tell that he is troubled. Most likely thinking about the deal. Time _**is**_ drawing to a close, so it wouldn't surprise her if his fear is starting to kick in. It's only human nature, after all. The gravity of the deal is finally hitting him and he feels hopeless and desperate at the same time. She can understand how he is feeling, even demons don't like being in hell.

She really shouldn't care about his fears, she isn't here for him after all, and his troubles aren't her problem. But she does care and she's seemingly making his troubles her problem and it's driving her crazy. She actually doesn't want to see him go to hell, doesn't want that to be his fate. He doesn't deserve it, no matter how selfish he was being when he made that deal.

These brothers need each other, every human and demon alike knows this. When Dean goes to hell, Sam is going to lose his mind with grief and despair. He isn't going to be the same person when all of this is said and done, Ruby can already see the changes in the younger hunter. He is going to be lost without Dean, will be more like a zombie than the bright hunter that he is.

Trouble is she knows just how lost Dean was when Sam had died. The emotional agony he went through is plain for her to see, he carries it with him even to this day. She knows he thinks he made the right choice by bringing Sam back and trading his own soul in return, and nothing anyone says is going to convince him otherwise. She wishes she could make him see how much weight and pain he's unwittingly placed on his younger brother, though.

She also wishes he would stop with this whole macho bullshit he's got going on. Facing hell with a cocky smirk, showing no fear, and all that. Its crap and they both know it. She wishes he would just be honest for once, stop hiding how he feels because she _**knows**_ he's scared. There's no way he can't be. But, yet, at the same time she's afraid for him to drop the mask because she isn't sure what will be left of him if he does.

When staring at him hunched in on himself with despair coming off of him in waves becomes too much to ignore any longer she steps out of the shadows and crosses the bridge till she's at his side. He doesn't say anything to acknowledge her presence but the sudden tenseness in his body gives him away.

"What do you want Ruby?" He asks with a heavy sigh, annoyance clear in the tone of his voice. "Don't you have better things to do than stalk me?"

"If I were to take the time and effort to stalk someone, Dean, it sure as hell wouldn't be you." She quips back because this is easy, this is something they know how to do and they do it well. Anything beyond that is foreign territory, uncomfortable and too close to anything real.

"Sam's back at the hotel, he's asleep but you could wake him up. I'm sure he'd _**love**_ to have you around." Dean snorts as he says this, glancing sideways at her and quirking an eyebrow. "Besides, what are you doing following me, anyway? He's the one you come around for, the sole reason you're even here, you don't have to bother yourself with me. Hell, I'd be thrilled to have you off my back."

"_**Aw**_, Dean, I'm beginning to think you don't like having me around, careful now you might hurt my feelings." Ruby rolls her eyes and moves to lean against the unsteady railing, watching his facial features intently. "Besides, why would I miss out on the chance to see you doing your best impression of emo-Sam?"

"Bite me," Dean grumbles and turns away, jaw clenching. "Now, why don't you fuck off and leave me the hell alone."

"Easy there, short bus, don't get your panties in a twist." Ruby can't help but smirk and the amusement in her voice is unmistakable. "I actually didn't come here to argue with you, as much fun as that is, I just came to talk."

"Yeah, well, I'm not in a talking kind of mood."

"Then shut up and listen, take some advice for once. You need to talk about what your feeling, Dean, or this is going to eat you alive. You're going to hell, not figuratively, literally!" She says in a harsher tone than she intends. "Now, I'm not usually one for heart to hearts or anything but I know what you're going through, you can talk to me about this if you want, or maybe you should talk to Sam. I don't care who you talk to, but you _**need**_ to talk to someone."

"Whatever, I don't have the patience for your shit right now Ruby, just go the hell away." Dean grits out, not even bothering to give her his trademark smirk, and promptly walks away, heading back down the dark and desolate dirt road that leads to the motel.

"You can't run from this forever, Dean," Ruby calls after him, silently smiling in satisfaction when he stops in his tracks.

Dean turns around and gives her a shit-eating grin, though it doesn't hold the sarcasm it usually does. "Maybe not, but I don't have to deal with it right now, and I sure as hell ain't spilling my guts to a _**demon**_,"

Dean turns once more and leaves Ruby behind, standing alone on the bridge, shaking her head solemnly. She isn't about to give up, though. She doesn't understand why she doesn't just write him off as a lost cause, but she just can't give up on him that easily.

۞ ۞ ۞

Once again she finds herself watching Dean and she doesn't know why. She had been discretely watching the diner from across the street, keeping an eye on Sam, telling herself she was only there for him. Which is exactly why she was there, that's ever the only reason she is around, to watch over Sam and make sure he doesn't get himself into any sticky situations that might get his dumbass killed.

That notion completely went out the window, however, the moment Dean stood up and left without his brother. Ruby was then caught in the decision of what to do now. Obviously she should stay where she is and do the job she came to do, which is watch over Sam, especially now that stupid ass Dean is leaving him alone.

But, in the end, that isn't what she did. No, instead she followed fuckin' Dean to this hole in the wall bar where he is currently trying to see if he can drown himself in alcohol. He is sitting at the far end of the bar, away from anyone that might think about striking up a drunken conversation, and lazily sloshing the liquid in the murky brown bottle.

Ruby stands off in a dark corner so as to not be seen but she gets the feeling that he can sense her presence, if the glances in her direction are anything to go by. She knows he can't see her, but it's obvious he can feel her eyes upon him and it's raising his hunter instincts.

Ruby is instantly alert when a skanky brunette bimbo sidles her way up to Dean, cocking a hip and giving him a sleazy come hither smile. Something primal and possessive inside of her releases a growl when Dean turns to the skank and gives her a leer of his own, unabashedly roaming his eyes over her body.

Before she even realizes what she's doing, Ruby strides over to them and plops down onto the stool next to Dean. He lets out a groan and hangs his head when he sees that she is the newest arrival.

"Ruby," he speaks her name in annoyance. "Why am I not surprised to see you here?"

"I have a knack of showing up at just the right moments." She grins falsely, propping her chin up with the palm of her hand and eyeing the bimbo on the other side of Dean dangerously.

"Shouldn't you be harassing Sam?" He asks. "What are you even doing here?"

"That's how you greet a friend, Dean?" She responds, trying her best to sound appalled. "You act like you're not even a bit happy to see me, you keep that up and you're gonna give me a complex."

"I'm not happy to see you," Dean grumbles, though Ruby thinks she can detect a bit of a smile in his voice that he is trying his damnedest to hide. An air of confusion surrounds him because of it and she can't help thinking, _I know how you feel_, with an ironic smile.

_So maybe this isn't one sided, he can feel this attraction too, whatever it means_, she thinks to herself, feeling pretty damn pleased for some strange reason.

"Don't lie to yourself, Dean, just admit it, you like having me around." She taunts him lightly, reaching out and taking a swig of his beer. "I do believe you're starting to like me."

Dean smirks at this. "I think you have that the other way around sister, after all, you're the one who can't seem to stay away. Every time I turn around you just happen to be there, I've almost come to expect it now."

"What can I say, I have a soft spot for the dark and brooding type." She responds with a casual shrug of her shoulders, hiding the fact that she is troubled because she thinks he just may have a point.

The skanky bimbo huffs when she realizes she isn't going to get anywhere with her target of the night and stomps off like a five year old, sulking the whole way. Ruby just smirks triumphantly and turns her attention to Dean who doesn't even seem to care that she cock-blocked him.

"So, where's Sam?" She asks, even though she already knows. "Why isn't he here having a beer with ya?"

"Left him at the diner," he shrugs carelessly. "He's heading over to the library to do some research afterwards and he'll be gone for a long time and I didn't feel like waiting around for him, too fuckin' boring."

Ruby wants to laugh at how casual their conversation is. Who knew that a hunter and a demon could sit down and chat like this. Kind of ironic, all things considered. She doesn't comment on this, though, content with sitting here with Dean and making casual small talk.

"This," she says indicating the bottle of beer she still has clutched in her hands, "tastes like piss."

"No one's asking you to drink it." He responds nonchalantly before snatching it out of her hands. "Besides, this one's mine, you want to drink piss flavored beer you get your own."

"I'll have to pass on that." She says with a disgusted upturn to her lips. "As nice as having a cold one with you in some shitty bar sounds, I'll have to take a rain check."

"Right," he drawls, not believing her for a second.

Sure, she might show up at a bar somewhere down the line, she can't seem to stay away from him as it is, but she isn't a beer type of demon. Just the thought makes her want to laugh at the irony of it. For the life of her she can't figure out why she is still here, why she doesn't just get up and walk away. She's a little surprised that Dean hasn't left, either. She never thought he'd willing sit here with her and have a normal conversation. _Guess he can still surprise me after all_, she thinks to herself.

"Why, Dean, I do believe you're starting to warm up to me." She teases, unable to help herself.

He deadpans. "Don't ruin it."

She grins secretly to herself but doesn't say anything more. After a few long moments of companionable silence she is growing restless, not accustomed to sitting in one place for such a long period of time. She watches as he rises from the stool and tosses down a couple dollars onto the bar. He mumbles, "I'm getting outta here, see ya 'round Ruby," and walks with a confident swagger out of the bar, leaving her sitting on the bar stool to look after him.

۞ ۞ ۞

She knows she has no business being here, should have left well enough alone when Dean left her behind at the bar, but she still finds herself here all the same. She vaguely wonders what he will do when he enters the motel room only to find her sitting casually on his bed. She's sure her presence won't be well received but, then again, when has she ever let that stop her?

Even _**she**_ doesn't know why she is here, waiting somewhat impatiently for the hunter to arrive. Wasn't hard for her to get in, either. The idiots forgot to lay down the salt, which she makes a mental note to berate him for. Sure, they aren't in any immanent danger; no need for the salt right now. But that isn't the point. Every hunter knows to expect the unexpected. This time it was only Ruby that broke in to their room, their friendly neighborhood demon, but next time it might not be her. They need to learn to be more careful in the future.

She looks up when the door slams open, banging against the wall, and smiles at Dean who has the colt trained on her. She gives an over-exaggerated wave and pastes a fake smile on her face. "Now, honey, how many times do I have to tell you it's rude to keep a girl waiting?" She asks tauntingly, fluttering her eyelashes mockingly.

"Damnit Ruby!" He exclaims in irritation as he lowers the colt and slams the door behind him, seething in barely contained anger as he tries to calm down. "What the hell are you doing here? You don't just break into peoples' rooms, I almost shot you! I would've, too, if I didn't realize it was only you and not something dangerous."

"Hey!" She bellows, offended by the insult. "I'm just as dangerous as the next demon, thank you very fuckin' much."

"You know what I mean." He grumbles as he walks further into the room, tossing the colt onto Sam's bed and dropping down into one of the chairs. He leans his elbows on his knees and levels an inquiring stare on her. "Now, answer my question, what are you doing here?"

"You know me, a glutton for your charming presence." She rolls her eyes as she says this, trying to hide the real reason why she is here, why she can't stay away from him. "I don't know why I waste my time on your worthless existence."

"I've been trying to figure out why you're always around, too, and I think I have a pretty good idea." He says with a serious expression on his face that tells her maybe now would be a good time to leave. This conversation is headed in a direction she'd rather not deal with right now.

She swiftly rises to her feet, heading for the door only to find Dean blocking her path, staring down at her with those intense emerald green eyes of his. "You don't think I see what's going on here? You think I'm really that naïve?" He laughs humorlessly as he backs her up against a wall. "All this following me around, showing up every time I turn around, and don't think I haven't noticed you watching me… you're attracted to me, and it's freaking you out 'cause you don't understand it."

Her breath hitches in her throat as anger and shame flows through her from having this thing that's been confusing her brought out into the open. She wants to deny it, wants to laugh in his face and tell him he couldn't be farther from the truth, but she knows she'd only be lying to herself. She is attracted to him, and that's the problem.

"Wow, I didn't know your ego could get any bigger, guess I shouldn't underestimate you, huh Dean?" She mocks him simply because she doesn't know what else to do.

"You tell me I can't run from my situation forever when you're doing the same damn thing… you're a fuckin' hypocrite." He growls in her face, looking at her like she disgusts him.

At that moment her rage boils over and she pushes him back with all her strength. He crashes into the opposite wall, letting out a groan of pain as he collapses, and plaster breaks and falls to the floor from the impact. She strides over to him, picks him up, and then promptly slams him back against the wall.

"Don't you dare use that shit against me, 'cause while I may be trying to help your sorry ass, I'm still a demon and it'd be wise if you didn't piss me off." She growls, eyes bottomless pits of inky blackness. "You push me too far and I just may kick your ass like you deserve."

"It's a bitch, isn't it?" He mocks her, looking at her with those damn eyes that have haunted her for days. "Having someone point out the truth isn't much fun, is it? You can dish it out but you obviously can't take it."

"You want to talk about truth, Dean? Fine, let's talk about the truth. Truth of the matter is you're going to hell in a few months, the weight of that is weighing heavy on your shoulders." She whispers harshly.

"Shut up," his voice is low and dangerous but she pays it no heed.

"You can't lie to me; I can see it there in your damn eyes. You're scared, hell, you're fuckin' terrified. But will the great Dean Winchester admit it? Hell no, why would he? That might make him less of a man, might break that mask he clings so hard to and then he couldn't hide anymore." She seethes in his face, watching as his lips twitch with rage, watches as it boils just below the surface along with all those fears he won't allow himself to show.

"Shut up, you bitch!" He yells as he pulls his fist back and hits her in the jaw.

She smiles in satisfaction as she rubs her aching jaw. "See, the difference between you and me is, I'm willing to admit to my attraction to you, won't even try to deny it, but you're so damn intent on running from your problems and laughing them off with a carefully placed smirk that it's getting to be pathetic.

No one will think less of you for being scared Dean, it's only natural. But you can't hide from this forever, it's happening whether you like it or not. The trick is to not lose that will to fight that you still have left in you. Once that's gone you're as good as dead, might as well throw in the towel right now."  
Ruby crowds Dean up against the wall as he speaks with fierce determination. "That fear is a good sign, you asshole, embrace it don't hide it. Shows you're still alive, that there's still fight in you and you're not gonna go down easily."

Ruby takes a step back once she is finished but keeps her eyes trained on Dean as he takes in her words. He stands there, chest heaving, eyes hardened by suppressed anger and fear, and she doesn't say a word, just gives him time to let it all sink in.

He catches her unaware and unprepared when he grips onto her arms, pulls her flush against him, and his lips attack hers with pent up frenzied need and lust. Inwardly, she's telling herself to push him away, hit him for even thinking he can kiss her like this, but what she finds herself doing is fisting her hands into his shirt and dragging him impossibly closer.

His mouth devours hers desperately and she gives up being pliant and begins to fight in earnest for dominance. Tongues tangle and slide wetly together, his hands find their way into her hair and pull harshly, just this side of painful, and she responds in kind by digging her nails into his shoulders, grasping and holding on as though for dear life.

He releases his hold on her hair when she begins tugging on his leather jacket and lets his arms hang loosely at his sides as she pushes it off his shoulders and it falls to the floor. He strips her of her jacket quickly and then their mouths are attached once more. Desire is flooding her system in waves unlike anything she has felt in a long, long time and she's almost dizzy with it.

They stumble further into the room, the backs of her knees hitting the end of the bed. She swiftly turns them before she falls, though, and pushes him down onto it. He looks up at her, slightly surprised by the quick movement, and his eyes darken as he takes in the sight of her. She eyes him salaciously as she grabs the hem of her shirt and draws it over her head, tossing the article of clothing behind her carelessly.

Slowly, Ruby climbs onto the bed and straddles Dean's waist, leaning down to capture those sinful lips with her own. They kiss passionately, recklessly, for a moment before she lifts up once more and draws Dean with her. He takes the hint when she tugs at the hem of his shirt and lifts his arms into the air. She quickly removes the offending material and her hands instantly seek out flesh.

He arches up into her wandering hands when she stops to rub a nipple. Her grin is sultry as she makes the decent to his chest and draws that nipple into her mouth, lavishing it with wet suction and swipes of her tongue. A deep rumbling groan is what she receives for her troubles and she thinks she could get used to hearing that sound more often. It's a good sound for him, after all.

She forces herself to pull away when she feels his hand on her and she lifts up to give him better access. He leers at her as he pulls her bra down and cups her breast in one of his hands. He caresses her far more tenderly than she expected from him but she doesn't complain in the slightest. She feels herself shudder when he rubs the pad of his thumb over her hardened nipple and gasps when he pulls her down, drawing her breast to his mouth and nipping it teasingly before putting his tongue to work.

Refusing to remain idle, she makes short work of his belt buckle and swiftly undoes his pants, slipping her hand inside and wrapping it around his length. She watches as his eyes roll back into his head and a low moan escapes his throat. The angle is odd, considering she is still straddling him, but she makes a great effort to stroke him generously. He seems to appreciate it, if the moans coming from his lips are anything to go by.

If she lets out a yelp when he suddenly grabs her and flips her over onto her back, she'll never admit it. She looks up at him as he leans over her and just **knows** the fun is about to begin.

۞ ۞ ۞

Dean sits quietly on the bed, still shirtless with beads of sweat sliding down his chest, as Ruby tugs her shirt back on. Her hair is a disarray of tangles and snarls. _I look like I just got good and laid_, she muses to herself humorously as she looks at her reflection in the mirror. Her hair is mused, she's looking a bit flushed, and her skin is still shiny with perspiration. She feels pretty damn good, though, she can't deny that.

Looking back at Dean she has half a mind to attack him again and go another round. She gains control over herself, though, and sits down across from him on Sam's bed instead. He meets her eyes briefly before they slide away and there is no mistaking the troubled look on his face. She recognizes it from that night on the bridge and instantly knows what he is thinking about.

He takes a deep breath and raises his eyes once more to lock onto her stare. "You're right… I'm scared." He finally admits, though it looks like it takes a great amount of strength to let go of his pride long enough for him for him to get the words out.

She should be happy that he is finally opening up a bit, finally admitting his fears and speaking them aloud, but all she feels is sympathetic and upset, for him. She knows what all of this is doing to him and, oddly enough, she wishes there was something she could do to help him through this. Nothing she can possibly say will make his situation any more bearable, though, so she keeps her mouth shut for once.

"I don't want to go to hell; I never wanted things to come to this. I don't want to leave Sammy here alone and I never meant to put any of this on his shoulders. I thought I was doing the right thing, and I still think I did the right thing, but I just wish it wasn't so hard." He sighs heavily and drops his head into his hands.

Cautiously, as though dealing with an abused animal, Ruby moves to sit beside him and cups his cheek. He raises his head a moment later and allows her to pull him into a kiss. She tries to reassure him with her lips, let him know he isn't alone in this anymore if he doesn't want to be, and he kisses her just a bit harder, so she thinks it's safe to assume her message has been received.

He pulls back a moment later to let some air into his lungs and looks at her with bright, expressive eyes. "I don't wanna die, Ruby, and I definitely don't wanna go to hell, but I've made my bed and now I gotta lie in it. It's just as simple as that. There's no way of getting out of this, not this time."

"Don't lose hope now, Dean. I'll kick your ass if you lie down and just accept this as your fate. It's not who you are and we both know it. There's gotta be a loop hole somewhere, and I'll find it. You're not going to hell, Dean, not if I have anything to say about it." She says patting his knee roughly before standing up and striding over to the door.

"Thought you said there's no saving me from the pit," he reminds her solemnly as he moves to stand with her at the door, looking unconvinced. She can tell he wants to believe her but just can't let himself.

"Yeah, well, I'll find a way. I don't care what it takes; I'll find a way to save you. As long as I'm still around to do something about it you won't be going to hell," she tells him firmly. What she doesn't say is, _"I can't let anything happen to you, I can't lose you now."_ because even she's a little messed up right now and doesn't understand this feeling coursing through her body, this attraction towards him.

Ruby leans into his personal space, kissing him deeply, and then she slips out the door. Leaving Dean standing there with a slightly dazed look in his eyes as the flame of hope reignites inside of him.

She's still confused about her own feelings, always figured she **couldn't** feel human emotions now that she's a demon, but she has bigger things to worry about at the moment. All she knows is she can't lose him; feels hollow and dead inside when she thinks about it. She'll have plenty of time to evaluate this foreign feeling, plenty of time to come to terms with it, but right now she needs to focus on finding a way to save Dean.

Even if she has to personally kill every demon that stands in her way, she will find a way to save him… there just can't be any other alternative.

**The End**


End file.
